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Title: Stereoselective reactions of N,N-dibenzyl protected synthons : applications to natural product synthesis
Author: Curley, Karen S.
Awarding Body: University of Edinburgh
Current Institution: University of Edinburgh
Date of Award: 2002
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The first part of this thesis describes the synthesis of TBDPS protected CYB-3 125 via a substrate controlled acetate aldol reaction of 93. A Claisen condensation reaction of the imidazolide 157 followed by a highly diastereoselective reduction enabled a synthesis of the C(3) epimer of TBDPS protected CYB-3 159. As a further demonstration of this methodology, the Claisen condensation reaction and reduction protocol was extended to the synthesis of b-hydroxyl alcohol 221. The synthesis of methyl ketone 244 has been reported utilising the conditions optimised for the synthesis of 93. Preliminary investigations of the aldol reaction of 244 with a range of achiral aldehydes have been conducted. Finally studies into an interesting cyclisation using iodoxybenzoic acid (IBX) 262 are discussed.
Supervisor: Not available Sponsor: Not available
Qualification Name: Thesis (Ph.D.) Qualification Level: Doctoral
EThOS ID:  DOI: Not available